List of tallest buildings in Winnipeg

Winnipeg is the capital and most populous city of the Canadian province of Manitoba, with a metropolitan population of over 830 thousand as of 2021. As Manitoba's largest city by far, Winnipeg contains the vast majority of high-rises in the province. As of 2026, Winnipeg has 24 buildings that stand taller than 75 m (246 ft), six of which are taller than 100 m (328 ft). Winnipeg's skyline is the third-largest in the Canadian Prairies, after Calgary and Edmonton. The tallest building in Winnipeg is 300 Main, a 141.7 m (465 ft) tall multi-family residential tower completed in 2022.

As Canada's third-largest city in the early 20th century, Winnipeg is home to some of Canada's first high-rises. The 11-story Union Bank Building, completed in 1904 for the Union Bank of Canada, is considered by some to be the first skyscraper in Canada. This early development boom was halted after the onset of World War I. Few high-rises were built between the 1920s and 1950s; from 1920 to 1969, the neoclassical Manitoba Legislative Building, the province's third legislative building, was the tallest structure in the city. A larger high-rise construction boom began in the 1960s and lasted until 1990, which saw the completion of office buildings such as the Richardson Building, 360 Main, and 201 Portage—the city's tallest building at 128 m (420 ft) from 1990 to 2022—and residential complexes such as Fort Garry Place and Holiday Towers.

Few tall buildings were completed in the 1990s and 2000s. A notable exception was Manitoba Hydro Place, the headquarters of Manitoba Hydro, an electric power and natural gas utility, in 2008. Another construction boom began in the 2010s. A significant recent project is True North Square, a public plaza and mixed-use development downtown. True North Square involves five towers spanning over 1 million square feet (93,000 m²) of office, residential, retail, hotel, and public space; three towers have been built as of 2026. In addition, 300 Main surpassed 201 Portage to become the city's tallest building in 2022.

Most high-rises in Winnipeg are situated in Downtown Winnipeg, which is bordered by the Red River to the east and the Assiniboine River to the south. Winnipeg's four tallest towers are located near each other, just south of the Exchange District. There are several residential towers in the Roslyn and Osborne Village neighbourhoods south of downtown. The tallest of these is 55 Nassau North, the city's sixth-tallest building. In addition to its high-rises, Winnipeg's skyline notable for Canadian Museum for Human Rights, which features a glass spire that reaches 100 m (328 ft) in height.